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Organocatalytic Regioselective Chlorosilylation of Oxirane Derivatives: Mild and Effective Insertion of Bulky Silyl Chloride by Using 4‐Methoxypyridine N ‐Oxide
Author(s) -
Yoshida Keisuke,
Suzuki Hina,
Inoue Hiroki,
Matsui Kohei,
Fujino Yuta,
Kanoko Yohei,
Itatsu Yukihiro,
Takao Kenichi
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600209
Subject(s) - chemistry , regioselectivity , silylation , chloride , reagent , organic chemistry , sodium , catalysis , medicinal chemistry , combinatorial chemistry
The highly regioselective organocatalytic chlorosilylation of oxirane derivatives using bulky silyl reagents such as ( tert ‐butyl)diphenylsilyl chloride (TBDPSCl) or triphenylsilyl chloride (Ph 3 SiCl) was developed. The reaction was effectively catalyzed with 4‐methoxypyridine N ‐oxide in the presence of sodium sulfate (Na 2 SO 4 ). Several silylated halohydrins were obtained with complete regioselectivity and the reaction was applied to the synthesis of carvedilol.